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3742-91-4

3742-91-4

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 37 Articles be found

Sustainable Route Toward N-Boc Amines: AuCl3/CuI-Catalyzed N-tert-butyloxycarbonylation of Amines at Room Temperature

Cao, Yanwei,He, Lin,Huang, Yang

, (2021/12/22)

N-tert-butoxycarbonyl (N-Boc) amines are useful intermediates in synthetic/medicinal chemistry. Traditionally, they are prepared via an indirect phosgene route with poor atom economy. Herein, a step- and atom-economic synthesis of N-Boc amines from amines, t-butanol, and CO was reported at room temperature. Notably, this N-tert-butyloxycarbonylation procedure utilized ready-made substrates, commercially available AuCl3/CuI as catalysts, and O2 from air as the sole oxidant. This catalytic system provided unique selectivity for N-Boc amines in good yields. More significantly, gram-scale preparation of medicinally important N-Boc amine intermediates was successfully implement, which demonstrated a potential application prospect in industrial syntheses. Furthermore, this approach also showed good compatibility with tertiary and other useful alcohols. Investigations of the mechanisms revealed that gold catalyzed the reaction and copper acted as electron transfer mediator in the catalytic cycle.

Cobalt-Catalyzed C(sp2)-C(sp3) Suzuki-Miyaura Cross Coupling

Ludwig, Jacob R.,Simmons, Eric M.,Wisniewski, Steven R.,Chirik, Paul J.

supporting information, (2020/11/02)

A cobalt-catalyzed method for the C(sp2)-C(sp3) Suzuki-Miyaura cross coupling of aryl boronic esters and alkyl bromides is described. Cobalt-ligand combinations were assayed with high-throughput experimentation, and cobalt(II) sources with trans-N,N′-dimethylcyclohexane-1,2-diamine (DMCyDA, L1) produced optimal yield and selectivity. The scope of this transformation encompassed steric and electronic diversity on the aryl boronate nucleophile as well as various levels of branching and synthetically valuable functionality on the electrophile. Radical trap experiments support the formation of electrophile-derived radicals during catalysis.

Photoredox catalysis on unactivated substrates with strongly reducing iridium photosensitizers

Shon, Jong-Hwa,Kim, Dooyoung,Rathnayake, Manjula D.,Sittel, Steven,Weaver, Jimmie,Teets, Thomas S.

, p. 4069 - 4078 (2021/04/06)

Photoredox catalysis has emerged as a powerful strategy in synthetic organic chemistry, but substrates that are difficult to reduce either require complex reaction conditions or are not amenable at all to photoredox transformations. In this work, we show that strong bis-cyclometalated iridium photoreductants with electron-rich β-diketiminate (NacNac) ancillary ligands enable high-yielding photoredox transformations of challenging substrates with very simple reaction conditions that require only a single sacrificial reagent. Using blue or green visible-light activation we demonstrate a variety of reactions, which include hydrodehalogenation, cyclization, intramolecular radical addition, and prenylationviaradical-mediated pathways, with optimized conditions that only require the photocatalyst and a sacrificial reductant/hydrogen atom donor. Many of these reactions involve organobromide and organochloride substrates which in the past have had limited utility in photoredox catalysis. This work paves the way for the continued expansion of the substrate scope in photoredox catalysis.

Desulfonylative Arylation of Redox-Active Alkyl Sulfones with Aryl Bromides

Hughes, Jonathan M. E.,Fier, Patrick S.

supporting information, p. 5650 - 5654 (2019/08/01)

We describe the development of the first reductive cross-electrophile coupling between alkyl sulfones and aryl bromides. The use of alkyl sulfones offers strategic advantages over other alkyl electrophiles as they can be incorporated into molecules in unique ways and permit α-functionalization prior to coupling. The conditions developed here enable incorporation of a wide array of aromatic rings onto (fluoro)alkyl scaffolds with broad functional group tolerance and generality, making this a practical method for late-stage diversification.

Orthoester in Cyclodehydration of Carbamate-Protected Amino Alcohols under Acidic Conditions

Park, Heemin,Kwon, Yongseok,Shin, Jae Eui,Kim, Woo-Jung,Hwang, Soonho,Lee, Seokwoo,Kim, Sanghee

, p. 2761 - 2767 (2017/06/13)

The first acid-promoted reaction system to form azaheterocycles from N -carbamate-protected amino alcohols is described. The reaction involves the activation of the hydroxyl group via the use of orthoesters. Despite the reduced nucleophilicity of carbamate nitrogen, this reaction system provides several types of pyrrolidines and piperidines in good to high yields. Using this protocol, prolinol derivatives can also be synthesized from carbamate-protected amino diols with regio- and stereoselectivity.

Process route upstream and downstream products

Process route

piperidine
110-89-4

piperidine

carbon dioxide
124-38-9,18923-20-1

carbon dioxide

benzyl chloride
100-44-7

benzyl chloride

N-(benzyloxycarbonyl)piperidine
3742-91-4

N-(benzyloxycarbonyl)piperidine

N-Benzylpiperidine
2905-56-8

N-Benzylpiperidine

Conditions
Conditions Yield
piperidine; carbon dioxide; With caesium carbonate; In N,N-dimethyl-formamide; at 23 ℃; for 0.75h;
benzyl chloride; In N,N-dimethyl-formamide; at 23 ℃; for 24h;
68%
32%
5-<(benzyloxycarbonyl)amino>pentanol
87905-98-4

5-<(benzyloxycarbonyl)amino>pentanol

N-(benzyloxycarbonyl)piperidine
3742-91-4

N-(benzyloxycarbonyl)piperidine

Conditions
Conditions Yield
With boron trifluoride diethyl etherate; orthobenzoic acid trimethyl ester; In dichloromethane; at 20 ℃; for 5h; Inert atmosphere; Reflux;
68%
piperidine
110-89-4

piperidine

benzyl chloroformate
501-53-1,94274-21-2

benzyl chloroformate

N-(benzyloxycarbonyl)piperidine
3742-91-4

N-(benzyloxycarbonyl)piperidine

Conditions
Conditions Yield
With sulfuric acid; silica gel; at 20 ℃; for 0.166667h;
94%
With potassium carbonate; In tetrahydrofuran; for 1h;
93%
With Amberlyst-15; at 20 ℃; for 0.166667h; Neat (no solvent);
92%
With dodecatungstophosphoric acid hydrate; In dichloromethane; at 20 ℃; for 0.166667h;
90%
With cetyltrimethylammonim bromide; In water; at 30 ℃; for 0.25h;
82%
In neat (no solvent); at 50 ℃; for 0.0666667h; chemoselective reaction; Microwave irradiation; Green chemistry;
82%
With dimethylbromosulphonium bromide; In toluene; at 20 ℃; for 0.25h;
76%
With pyridine; HOBT bound to the polystyrene-divinylbenzene copolymer resin; Yield given. Multistep reaction; 1.) CH2Cl2, 25 deg C, 2.) CH2Cl2, 25 deg C;
With sodium hydroxide; In water; at 0 - 20 ℃;
With diethyl ether;
benzyl chloroformate
501-53-1,94274-21-2

benzyl chloroformate

N-(benzyloxycarbonyl)piperidine
3742-91-4

N-(benzyloxycarbonyl)piperidine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 87 percent / triethylamine / CHCl3 / 1 h / 20 °C
2: 83 percent / triethylamine / tetrahydrofuran / 1 h / 20 °C
With triethylamine; In tetrahydrofuran; chloroform;
Multi-step reaction with 2 steps
1: 83 percent
2: 93 percent / dimethylformamide / 1 h / Ambient temperature
In N,N-dimethyl-formamide;
With potassium carbonate; Rh/C; In tetrahydrofuran; ethanol;
4.6 g (76%)
With potassium carbonate; Rh/C; In tetrahydrofuran; ethanol;
4.6 g (76%)
With potassium carbonate; Rh/C; In tetrahydrofuran; ethanol;
4.6 g (76%)
Multi-step reaction with 2 steps
1: dichloromethane
2: acetonitrile / 25 °C
In dichloromethane; acetonitrile;
benzyl 4-bromo-1-piperidinecarboxylate
166953-64-6

benzyl 4-bromo-1-piperidinecarboxylate

N-(benzyloxycarbonyl)piperidine
3742-91-4

N-(benzyloxycarbonyl)piperidine

Conditions
Conditions Yield
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; tris-(trimethylsilyl)silane; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 10h; Irradiation;
91%
With 1,3-dimethyl-2-phenyl-2,3-dihydro-1H-benzo[d]imidazole; C41H39IrN6; In acetonitrile; at 45 ℃; for 24h; Reagent/catalyst; Irradiation; Glovebox;
80%
piperidine
110-89-4

piperidine

carbon monoxide
201230-82-2

carbon monoxide

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

N-(benzyloxycarbonyl)piperidine
3742-91-4

N-(benzyloxycarbonyl)piperidine

Conditions
Conditions Yield
With gold(III) chloride; copper(l) iodide; at 20 ℃; for 24h; under 750.075 - 3000.3 Torr;
94%
benzyl (2-bromoethyl)(3-bromopropyl)carbamate

benzyl (2-bromoethyl)(3-bromopropyl)carbamate

N-(benzyloxycarbonyl)piperidine
3742-91-4

N-(benzyloxycarbonyl)piperidine

Conditions
Conditions Yield
With nickel(II) iodide; [2,2]bipyridinyl; zinc; In N,N-dimethyl acetamide; at 25 ℃; for 16h; Schlenk technique; Inert atmosphere;
50%
piperidine
110-89-4

piperidine

benzyl (1-chloroethyl) carbonate
99464-81-0

benzyl (1-chloroethyl) carbonate

N-(benzyloxycarbonyl)piperidine
3742-91-4

N-(benzyloxycarbonyl)piperidine

Conditions
Conditions Yield
With potassium carbonate; In tetrahydrofuran; at 20 ℃;
97%
piperidine
110-89-4

piperidine

N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

N-(benzyloxycarbonyl)piperidine
3742-91-4

N-(benzyloxycarbonyl)piperidine

Conditions
Conditions Yield
With 1-butyl-3-methylimidazolium Tetrafluoroborate; In neat (no solvent); at 25 ℃; for 0.05h;
95%
piperidine
110-89-4

piperidine

benzyl 4,6-dimethoxy-1,3,5-triazinyl carbonate
419533-86-1

benzyl 4,6-dimethoxy-1,3,5-triazinyl carbonate

N-(benzyloxycarbonyl)piperidine
3742-91-4

N-(benzyloxycarbonyl)piperidine

Conditions
Conditions Yield
With triethylamine; In tetrahydrofuran; at 20 ℃; for 1h;
83%

Global suppliers and manufacturers

Global( 6) Suppliers
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  • SAGECHEM LIMITED
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-571-86818502
  • Emails:will@sagechem.com
  • Main Products:28
  • Country:China (Mainland)
  • Chemical Co.Ltd
  • Business Type:Trading Company
  • Contact Tel:
  • Emails:zhang@163678.com
  • Main Products:1
  • Country:China (Mainland)
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